S$ 611 Find Cheap Flights from Chicago to Singapore

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Singapore departing on 27-7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Chicago to Singapore

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to Singapore that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to Singapore

Tue, 8 Sep - Tue, 29 Sep
Turkish Airlines Logo
20:10 - 08:45
ORD
-
SIN
23h 35m
1 stop
Turkish Airlines Logo
10:25 - 09:40
SIN
-
ORD
36h 15m
1 stop
S$ 1,236Turkish Airlines
Mon, 24 Aug - Mon, 14 Sep
Cathay Pacific Logo
16:00 - 15:40
ORD
-
SIN
34h 40m
1 stop
Cathay Pacific Logo
09:45 - 14:20
SIN
-
ORD
41h 35m
1 stop
S$ 1,247Cathay Pacific
Mon, 24 Aug - Mon, 14 Sep
Cathay Pacific Logo
16:00 - 15:40
ORD
-
SIN
34h 40m
1 stop
Cathay Pacific Logo
20:05 - 14:20
SIN
-
ORD
31h 15m
1 stop
S$ 1,248Cathay Pacific
Tue, 8 Sep - Tue, 29 Sep
Air Canada Logo
15:40 - 05:15
ORD
-
SIN
24h 35m
1 stop
Air Canada Logo
07:00 - 09:43
SIN
-
ORD
39h 43m
2 stops
S$ 1,262Air Canada
Tue, 8 Sep - Tue, 29 Sep
Air Canada Logo
06:00 - 05:15
ORD
-
SIN
34h 15m
2 stops
Air Canada Logo
07:00 - 09:43
SIN
-
ORD
39h 43m
2 stops
S$ 1,268Air Canada
Wed, 14 Oct - Sun, 25 Oct
Delta Logo
09:55 - 05:00
MDW
-
SIN
30h 05m
2 stops
Delta Logo
22:30 - 18:37
SIN
-
MDW
33h 07m
2 stops
S$ 1,571Delta
Sat, 22 Aug - Fri, 28 Aug
Delta Logo
09:20 - 05:00
MDW
-
SIN
30h 40m
2 stops
Delta Logo
07:30 - 21:46
SIN
-
MDW
27h 16m
2 stops
S$ 1,603Delta
Wed, 13 May - Fri, 15 May
Multiple Airlines Logo
09:23 - 23:55
MDW
-
SIN
25h 32m
2 stops
Multiple Airlines Logo
01:25 - 12:42
SIN
-
MDW
24h 17m
2 stops
S$ 1,928Multiple Airlines
Wed, 13 May - Tue, 19 May
Korean Air Logo
09:23 - 19:15
MDW
-
SIN
44h 52m
2 stops
Korean Air Logo
22:00 - 12:42
SIN
-
MDW
27h 42m
2 stops
S$ 1,961Korean Air
Mon, 11 May - Sun, 24 May
Korean Air Logo
09:22 - 23:55
MDW
-
SIN
25h 33m
2 stops
Korean Air Logo
01:25 - 12:42
SIN
-
MDW
24h 17m
2 stops
S$ 1,969Korean Air
Booking Insights

KAYAK's insights & trends for Chicago to Singapore flights

Get data-powered insights and trends into flights from Chicago to Singapore to help you find the cheapest flights, the best time to fly, and much more.

What is the cheapest month to fly from Chicago to Singapore?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Singapore is January, when tickets cost S$ 629 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of return tickets is S$ 1,119 and S$ 1,079 respectively.

How far in advance should I book a flight from Chicago to Singapore?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on the flight from Chicago to Singapore, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 1 week before departure.

Good to know

Low seasonApril
Cheapest flightS$ 611
Best time to beat the crowds (11% less expensive on average)
Most popular time to fly (72% more expensive on average)
Flight from Chicago O'Hare Airport to Singapore

FAQs - booking Singapore flights

  • How does KAYAK find such low prices on flights from Chicago to Singapore?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Singapore.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Singapore?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Singapore is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Singapore?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly from Chicago to Singapore with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Singapore?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Singapore up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Singapore

 
Need help choosing which airline to fly with from Chicago to Singapore? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
Turkish AirlinesOverall score based on 4346 reviews
7.5Food
7.5Entertainment
7.8Crew
7.3Comfort
7.3Boarding
Airline reviews

The ground crew members at check in counter were courteous. The boarding was seamless. Flight departed as scheduled. Service on board was great

10.0 ExcellentOmo, Apr 2026
IAH - IST
Read more Turkish Airlines reviews

The ground crew members at check in counter were courteous. The boarding was seamless. Flight departed as scheduled. Service on board was great

Very comfortable in business class. Excellent service. Good food. Smooth trip.

The seats seems abit small and the reclining is too much, the seat in front of me came back too much and made it uncomfortable for me.

As a first time flyer with Turkish Airlines. My experience was very good due to the factor that there were to many passengers on the my first flight compared to my connecting flight. However, I know that nothing is perfect and all companies are trying to accommodate their passengers to the best way possible. I will always say, a FEW INCHES will go LONG WAY. That's something all airliners should consider, and not only the money aspect!!! A long time commitment is better than one time service! Thank you

Flight was delayed. While standing at the gate, a note appeared on the sign saying the gate had changed to a gate far away. No member of the Turkish airlines team got on the microphone to instruct passengers to go to the other gate, to ignore the chiron, etc. Finally, the message disappeared. Eventually, the flight began to board. Very slowly. More slowly than I experience with other airlines. Though Istanbul may just be slow . . . In all other ways, great flight, great entertainment (top notch movies), great service, excellent food, comfortable lie-flat seat, dimmed lights, etc.

Staff at the airport wasn't helpful or friendly. Probably the worst airport experience I have ever had, going and coming. The staff on the plane was better. Still not super friendly or personable. However, they were not rude like airport staff. They ran out of certain menu items. Maybe could have been prepared better? Overall just ok.

It was a pleasant experience. In flight entertainment could have been better

The desk crew at the LAX crew could do better. A girl named Mahesi was very abrasive and unfriendly. She needs a better customer service uproar.

It was peaceful excited We enjoyed it always Turkish peaceful excited

Istanbul to Lahore flight was less than standard for international business class cabins. Seat did not were not flat and it did not operate easily. I had to push buttons hard repeatedly to operate the seat. I was in 5A seat

1 hour delay meant missed my connecting flight and 1st day of holiday

The seats seemed smaller than other business class offerings. The entertainment menu was limited. Flight crew was good.

Dear Team, I purchased a full travel package that included 2 checked bags through you and JustFly. However, when I arrived at the airport, my ticket showed 0 checked bags. Since I was traveling internationally to India with 2 bags, It was a $200 per bag at the counter, which was extremely disappointing. For an international trip, why would I ever choose a no‑bag option for only $20–$30 less? This seems like an error in the booking process, and I am requesting clarification and a resolution. I have called JustFly and on phone for 1 hr :53 min and they couldn't help till I show some kind of proof etc which isn't possible but besides that love your service and using it for years !

Good one but just notice that you have to ask several time to get water or coffee .

The flight was over 1 hour late taking off ,when I arrived in Abu Dhabi ,I missed my connecting flight to Bangkok so I had to wait almost 6 hours for my flight arriving in Bangkok at 6:30 am ,So I missed a whole day of my vacation and my hotel room sat empty so I paid for hotel days that I was not there. In Abu Dhabi there was a woman that worked the desk at transfers that was so professional, courteous , helpful,and may I say absolutely beautiful .she got me food vouchers for my layover and was a very calming presence. Besides that I will never use Etihad again I will pay the Xtra money . I'm sure they won't read or see this but it's my "2 cents" I'll use an airline that respects me and my hard earned dollars

On this flight...fine. The one from India to Abu Dahbi, awful.

I booked and paid for a Business Class seat for myself and my wife. 4 hours before the flight i get a call saying the plane they sent doesn't have the correct layout to accommodate all the business class seats they sold me 3 months earlier at a premium of $1500 a ticket. So they have to bump me from Business to Economy and will give me a $400 credit (total of $800 for both seats) that I could turn in at Abu Dahbi for $400 in US cash. They then promised a row that we could have to ourselves and the arm rests would go up so we could spread out for each of us. My wife was taken care of but I was put in the exit row with the flight attendents set as part of the three...and the arm rest did not go up. When we got to Abu Dahbi, they would not exchange our credit for cash as promised. Very disappointed they took my money 3 months ago and refused to reimburse for the change in seats or follow the promises made.

It was fantastic. The flight from Chicago to Abu Dahbi was fantastic. The crew, food and service were amazing. Everything was handled by the crew member assigned to us , Nicholas, was usually done before we asked for it. Highly recommend Etihad!

I missed my flight ,staff unhelpful, they sat and watched me wait ,gangway door closed, English was a problem no announcement I was on time now I missed my month vacation ,lost 1400 bucks no refund I'm sick to my stomach

It’s a business class ticket but they didn’t give a lounge access

Everything you need to know for your flight from Chicago to Singapore

Cabin class types available on flights to Singapore

Cabin classes available on flights to Singapore. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.